4-(diethylaminomethyl)aniline → HCID 178463929, compound

HRID 641056Notes

Reaction equation

HRID 641056 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].O[CH:15]=[C:16]1[C:24]2[C:19](=[CH:20][C:21]([C:25]([C:27]3[CH:28]=[C:29]([NH:33][C:34]([C:36]4[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=4)=[O:35])[CH:30]=[CH:31][CH:32]=3)=[O:26])=[CH:22][CH:23]=2)[NH:18][C:17]1=[O:43]>C1COCC1>[CH2:1]([N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([NH:11]/[CH:15]=[C:16]2\[C:17](=[O:43])[NH:18][C:19]3[C:24]\2=[CH:23][CH:22]=[C:21]([C:25]([C:27]2[CH:28]=[C:29]([NH:33][C:34]([C:36]4[N:40]([CH3:41])[N:39]=[C:38]([CH3:42])[CH:37]=4)=[O:35])[CH:30]=[CH:31][CH:32]=2)=[O:26])[CH:20]=3)=[CH:12][CH:13]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 2368034-(diethylaminomethyl)anilineHCID 178426964HCID 178426964, compound

Product 1

HCID 178463929HCID 178463929, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-((diethylamino)methyl)aniline (A-04; 100 mg, 0.25 mmol, 1 equivalent) and N-(3-(3-(hydroxymethylene)-2-oxoindoline-6-carbonyl)phenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (Scaffold S1; 50 mg, 0.25 mmol, 1 equivalent) was taken in anhydrous THF (2 mL, 0.125 M) and heated at 70° C. for 16 h. Solvent was evaporated under vacuum and the crude product was purified by preparative RP-HPLC. 2,5-Dimethyl-2H-pyrazole-3-carboxylic acid (3-{3-[1-(4-diethylaminomethyl-phenylamino)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indole-6-carbonyl}-phenyl)-amide (78 mg, 55%) was obtained as a brown powder.

Workup

  1. customSolvent was evaporated under vacuum
  2. customthe crude product was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-ed303eb794b144c2be15257d602023fb
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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